2-Arachidonyl glycerol ether (CHEM041413)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:28:26 UTC
Update Date2016-11-09 01:22:28 UTC
Accession NumberCHEM041413
Identification
Common Name2-Arachidonyl glycerol ether
ClassSmall Molecule
DescriptionA monoalkylglycerol that is glycerol which is substituted by a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl group at position 2.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,8Z,11Z,14Z)-Icosatetraenyl-2-glyceryl etherChEBI
2-(5Z,8Z,11Z,14Z-Eicosatetraenyl)-sn-glycerolChEBI
2-AG etherChEBI
2-O-(5Z,8Z,11Z,14Z)-EicosatetraenylglycerolChEBI
5Z,8Z,11Z,14Z-Eicosatetraen-2-glyceryl etherChEBI
Noladin etherChEBI
2-Arachidonyl glyceryl etherMeSH
2-ArachidonylglycerolChEBI, HMDB
HU-310HMDB
NoladinHMDB
Chemical FormulaC23H40O3
Average Molecular Mass364.562 g/mol
Monoisotopic Mass364.298 g/mol
CAS Registry Number222723-55-9
IUPAC Name2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol
Traditional Name2-arachidonyl-glycerol
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CO)CO
InChI IdentifierInChI=1S/C23H40O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26-23(21-24)22-25/h6-7,9-10,12-13,15-16,23-25H,2-5,8,11,14,17-22H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI KeyCUJUUWXZAQHCNC-DOFZRALJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassEndocannabinoids
Sub ClassNot Available
Direct ParentEndocannabinoids
Alternative Parents
Substituents
  • 2-arachidonylglyceryl-ether-skeleton
  • Monoalkylglycerol
  • Monoradylglycerol
  • Glycerolipid
  • Glycerol ether
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP6.13ALOGPS
logP5.79ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity117.22 m³·mol⁻¹ChemAxon
Polarizability45.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c0-9152000000-4f071d1ae17fba4da471Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4290300000-e1b0c85cf9253f3d9540Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-4149000000-e4720c0dc226c8f75c6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-9552000000-acc6ac79c25f7b01fabcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adi-9530000000-f3e8c4232a41b271712dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4019000000-c1d518d9dd0e72949b1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9014000000-d9fb7a4798c72d74ca06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9010000000-a278d030fcbae6839865Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abc-9001000000-cd0050820da64ef90ba7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9010000000-7045d2ee77595c5503b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9020000000-84b3341a3a8edfdd26caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0100-9475000000-1098e6232c1c00d8484dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9421000000-67ab03b66d2ae0920375Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067m-9200000000-d2ec4200655bc27e732fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013657
FooDB IDFDB029627
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2-Arachidonyl_glyceryl_ether
Chemspider ID4983515
ChEBI ID75913
PubChem Compound ID6483057
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11259648
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22309979
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22728691
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23386378
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. The lipid handbook with CD-ROM